Toward the Rational Design of Sustainable Hair Dyes Using Cheminformatics Approaches: Step 2. Identification of Hair Dye Substance Database Analogs in the Max Weaver Dye Library
| Autor: | George Van Den Driessche, Denis Fourches, Tova N. Williams, Alain R. B. Valery, Harold S. Freeman |
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| Rok vydání: | 2018 |
| Předmět: |
Orange 1
010405 organic chemistry Renewable Energy Sustainability and the Environment General Chemical Engineering Skin sensitization Rational design General Chemistry 010402 general chemistry 01 natural sciences Combinatorial chemistry 0104 chemical sciences chemistry.chemical_compound chemistry Cheminformatics Dye uptake Hair dyes Environmental Chemistry |
| Zdroj: | ACS Sustainable Chemistry & Engineering. 6:14248-14256 |
| ISSN: | 2168-0485 |
| Popis: | We report on part 2 of the cheminformatics-assisted development of sustainable hair dyes with enhanced technical and toxicological properties. In this study, an initial similarity search analysis was performed using two reference probes (C.I. Basic Orange 1 and Orange 2) as structural templates for the identification of potential analogs among the Max Weaver Dye Library (MWDL). The analysis revealed an interesting subset of 158 MWDL compounds that were close analogs of the classical aminoazobenzene dyes. A more detailed similarity search analysis of this subset ultimately led to the selection of four dyes for further in silico quantum calculations and experimental dye uptake (color depth on hair) studies. Results from quantum calculations indicated that the ESP surface properties of these dyes were consistent with nonionic interactions between dye and keratin. Among the four dye analogs, 2-amino-6-methyl-5-(phenyldiazenyl)pyrimidin-4-ol and 2-amino-4-chloro-1,6-dimethyl-5-(phenyldiazenyl)-pyrimidin-1-ium ... |
| Databáze: | OpenAIRE |
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